Matchmaker
by LoveStory-Fanatic
Summary: AU: Dean owns a bar called The Roadhouse Bar & Grille near where Sam's going to Stanford. They found their own little family, but it's about to get bigger. Dean decides he needs to hire a new bartender. After a while, the new bartender decides to give himself the title of Matchmaker. He recruits some helpers and gets to work. Destiel/Sabriel
1. Wincestrial Love, Sweet Tooth, and Geeks

**Disclaimer: I do not own SPN. Nope.**

**Notes: Okay, soo...I've had the idea for this story for a while now. I couldn't take it anymore and decided to give it a shot. I hope you like it! Oh..and I'm just going to throw this out there that I am a pro-destiel person. Just thought I'd say that in case there is some confusion later in the chapter. Thanks!**

**Chapter 1**

The Roadhouse Bar & Grille. It was the name of the bar Dean Winchester owned. It was his pride and joy, apart from his little brother Sammy, of course. He'd bought the building when it was nothing but studs and had built it from the inside out. He'd given the place his own touch. It was his home away from home.

Dean and Sam had moved from their hometown of Lawrence, Kansas a few years ago when Sam had graduated from high school and been accepted into Stanford. While Sam lived in a dorm on campus, Dean lived in a small house he rented in Mountain View, California. It wasn't much, but it gave him space, privacy, and it was close to the bar.

When he'd put out advertisements looking for employees, he hit the jackpot. He found people who soon became his family. There was Ellen, the mother of the group. She worked most days and some nights, depending on the schedule and what needed to be done. Jo, Ellen's daughter, was the waitress. She was like a little sister to Dean. There was Ash who did the books. He called himself Dr. Badass and Dean swore he lived twenty years in the past due to his mullet and fashion sense. They also had Benny. He was the cook, the new addition to their family. Dean had hired him a couple of months previous and the two men were already practically brothers.

Recently, Dean had been overworking himself. He would push himself to his absolute limits. The Roadhouse was quite popular and they only had him and Ellen to work behind the bar. Dean worked every night of the week for months. He would also come in earlier than needed to make sure everything was good to go for that night. He didn't get much sleep, living on an average of four hours per night, sometimes less. He'd gotten into the habit of passing out on a small couch he had in his office instead of going home after the bar was closed and cleaned.

He'd gotten away with it for two weeks before Ellen had caught him and forced him to go home for a proper night's sleep. Ever since then, all of them, including Sam and Bobby, Ellen's husband, had been trying to convince him to put out another ad and hire a bartender. They were too short staffed to remain the way they were. Dean was worried to bring in someone else, an outsider into their family, but he didn't tell them that. They'd tried bringing in people before, but it never ended well. There had been Uriel, a frat kid who would sell to minors and almost got Dean into some serious trouble. There was Zach, a know-it-all who would frequently scare away customers. He'd almost single-handedly driven Dean out of business. Then there was a guy named Lucifer…Well, that was Sam's nickname for him. His real name was Mark. He had started to stalk Sam. At first it hadn't been anything real serious, nothing to worry about. Then Mark started showing up at Stanford unannounced. He would frequently call and text Sam, no matter the time of day. He even showed up at his dorm room several times. No matter what Sam did to tell the guy he wasn't interested, Mark just didn't get it.

Dean hadn't been aware of the issue for the first month it was going on. He'd been too focused on the bar, making sure everything was going smoothly. And, to be frank, the two brothers didn't get a lot of time to see each other until Sam turned twenty-one. When Dean found out about the stalking issue, he'd pulled Mark aside and told him that if he didn't leave his brother alone he'd have to let him go. That was that. The stalking stopped for a couple of days, long enough for Sam to relax. That's when the threats came. Sam started receiving letters under his door, calls from a blocked number, texts from a number he didn't recognize. He hadn't seen the point in alerting Dean, he thought he could handle it. One night, Sam stayed over at Dean's house as he frequently did on the weekends. His phone constantly went off while he was asleep, so Dean checked it to make sure it wasn't anything important. Dean found the threatening messages, the warnings. He never was a morning person, but that morning they all swear it was like watching a mama bear get provoked with a young cub: not pretty.

Dean waited until Sam got up, reading each text, getting angrier and angrier. He'd called Jo over to help him wrap his mind around it. When she'd shown up and seen how angry he was, she called in reinforcements. She'd called Ellen, Bobby, and Benny to Dean's house to help calm things down, hoping with most of the family there it wouldn't be a complete disaster.

Dean had shown them all the texts, all the threats, the warnings. They understood why he was upset. So, they waited for Sam to wake up. When he did, he was confronted for not telling anyone about the texts. Sam saw the worry and the hurt in Dean's eyes and immediately regretted it. He'd only hid it because Dean had enough on his plate, but that's what big brothers are for. Of course, Dean made him report the threats and they later found out that it had been Mark who was sending them from a new phone. Sufficed to say, he no longer had a job and there was a restraining order put on him.

That was the last time Dean had ever hired anyone new. That was also why it was a challenge getting him to put up an ad. Eventually, it worked. With enough pushing, nagging, long hours, sleepless nights, it finally broke through Dean's wall of stubbornness and he relented. So, that's where we are now. Dean received several applications and had sifted through them one day before the bar had any customers.

* * *

Dean was sitting in a booth, eating his lunch flipping through applications. He'd been meaning to look them over for a couple of days, but it'd been busy. This was the first chance he'd had. Benny was cleaning the grill for later and Jo was reading a book since they had no customers.

Jo looked up once she finished a chapter and her eyes shifted over to Dean. He was eating a fry and reading over an application. "Hey, Dean! Got any good ones yet?"

He nodded absently. "Maybe."

She stood from her spot at the bar and walked over to his booth, plopping down on the other side. "You know, they don't have to be perfect. And besides, you're going to interview them anyway before you hire them. Just pick some and call them in."

Dean sighed, running a hand over his face. "Fine. There are three that I'll even consider hiring. One guy and two chicks. Charlie Bradbury, Gabriel Coleman, and Becky Rosen. Their applications look good. We'll have to see what their interviews are like."

A smile appeared on her face. "Awesome! Call them! Set up times! But make sure I'm here. I want to meet them."

Dean rolled his eyes as he pulled out his phone. He got to work on setting up interview times for each of them. The first one was Becky's and it was in one hour.

"Okay. You have one hour before she shows up. Get to work and make this place presentable, would ya?"

She raised an eyebrow at him. "Dean. This place _is _presentable. It's practically spotless. There have been hardly any customers so far today so there hasn't exactly been too many messes to clean up."

Dean shook his head before gathering up the applications, his plate, and beer. "Yeah. Okay, well, I'll be in my office so when she shows up, bring her back."

He stood and walked into the kitchen where he deposited his plate before heading into his office. He tidied up some, made it look presentable. Truth was, he didn't use his office that much besides when he slept and when Ash did the books. He left it open for them to leave stuff in there in case they didn't want to carry something around all night. Benny frequently left his wallet in there as well as his motorcycle helmet and gloves. Occasionally, Bobby would come in and use the internet for some kind of research. Dean never asked and Bobby never told.

He still had a good fifteen minutes before she was due to show up, so he pulled out his phone and called Sam. It rang a few times before his little brother's voice came over the line.

"Hey, Dean, what's up?"

"Not a whole lot. Just killing time before someone comes in for an interview."

"Interview? You finally sat down and looked over those apps? Any good ones pop out?"

Dean glanced over at the three he'd selected. "Yeah, three of them. Charlie Bradbury, Becky Rosen, and Gabriel Coleman. Any of them sound familiar?"

There was a moment of silence as Sam seemed to think about the names. "The name Gabriel sounds familiar, but I can't think of where I heard it from. But I have no idea on the other two. How many are you hiring? Just the one or are you going for two?"

"I have no idea. It depends on how the interviews go, I guess. I'm probably only hiring one, but…Jo kindly pointed out to me earlier that she's the only waitress. So, we'll see how things go, I guess."

"Yeah. Another waitress couldn't hurt. Jo's doing pretty damn good by herself, but…she does get pretty stressed out most nights when it gets hectic. You may save her some premature grey hairs."

Dean chuckled, "Well, in that case, I'll let her suck it up. Hey, speaking of, are you going to be stopping by today?"

"Yeah, I'll be there in about fourty-five minutes. I'm waiting for the bus now."

Dean nodded, "Awesome. Well, maybe you'll catch a peak of the first girl. It's almost time for her to be showing up, so I'll let you go. I'll see you soon, Sammy."

He hung up the phone without waiting to hear his brother's response. He opened his laptop and brought up the budget for the month. He looked it over, making mental notes of his limits for the month. He'd completely engrossed himself in the budget, he didn't hear Jo walk in.

"Dean?"

His head snapped up and he noticed that Jo was standing there with someone behind him. "Sorry, wasn't paying attention."

She rolled her eyes before stepping aside, ushering someone in. "Dean, this is Becky Rosen. Becky, this is the boss, Dean Winchester."

Dean stood and extended his hand. They shook and he smiled politely. "Nice to meet you."

She seemed like a nice young girl. Nothing popped out at Dean immediately, but there was still time.

Jo left the office, closing the door behind her. Dean knew that she was standing right outside the door with Benny listening to the interview.

"So, Becky, what kind of position are you looking for?"

She smiled sweetly at him. "Waitress would be fine, but I'm open for anything." She sent a wink his way and he gulped. He already didn't like where this was going. He sat up straight and folded his hands together on the desk.

"What is your schedule like?"

"I'm free anytime you need me."

Dean nodded, "Okay. Well, for waitressing I'm only looking for someone for part-time. It would mainly be for the weekends, special events, and a couple of nights during the week. It wouldn't be too many hours."

She nodded, her smile growing. "That's perfectly fine! You see, that gives me plenty of time for my writing."

Dean smiled softly. "You're a writer?"

She nodded frantically. "Oh, yes. I write all the time. My goal is to be an author and I know I will be soon. I can just feel it. My ex-boyfriend is a published author, so he gave me some pointers."

Dean nodded, trying to seem interested and bring out her character, so who she really was. "Awesome. What kind of stuff do you write?"

"Oh, you know. I mainly write fanfiction. I write about these two brothers who are on this road trip across the country. They fight monsters and demons and save the world all the time. They're not recognized though, no one knows all the good they do for the world besides their family and the other hunters like them. Of course, everyone they know dies inevitably, so it has a lot of bromance and tears. It's a lot of fun to write. But it's not as much fun to write as when they go back to their motel room after a long, tiring hunt, slam each other against the wall, and make them theirs. It's so passionate! The love they have for each other is so inspiring. It truly is a better love story than Twilight, I don't care what anyone says! But then…there's this angel, right? He saves the older brother from Hell and then he decides to stick around. He gets in between the two brothers and makes the older one fall for him. I mean, really? How pathetic is that. They belong with each other, not him with this angel dude. It's called Wincest for a reason!"

"I'm sorry, Win-Wincest?"

Becky kept rambling as if she hadn't heard him. "I mean, really! They belong together, right? They've known each other their whole lives! The older brother practically raised his little brother after their mom died when a demon roasted her on the ceiling! And their dad…well…their dad went all big and bad hunter, so the older brother was a single parent. But, I'm getting off-track here. The younger brother gets tired of the angel, so he slams his brother against the wall and presses his lips to his neck, trailing hot kisses all the way down as he's ripping his brothers clothes off of him, trying to make him forget about the angel. So, the angel makes the older brother fall in love with him and then they get together. Well, not right away. Over the course of a few years they go back and forth with their feelings and hurting each other and all that, while the two brothers are also hurting each other. The poor little brother…he didn't ask for any of this…he just wants someone to love him. But…in the end the angel wins and they get together. They fall in love and yada yada yada. The little brother is left alone which is wrong. They fell in love first. They belong together! Am I right?"

Dean sat there staring at her, his lips parted slightly. He wasn't exactly sure what to say. "They're brothers? In love?"

Becky nodded enthusiastically, "Yep! They belong together!"

Dean nodded slowly. "Yeah, okay. Well, I think I've got all that I need. I have two other people coming in for an interview. I'll give you a call in the next couple of days to let you know the status of your application."

Becky's smile brightened. "Awesome! Thank you so much, Dean! I'm looking forward to hearing from you!"

Dean nodded and stood to walk her out. "Yeah. Me too."

They walked out of the office and Dean saw Benny and Jo giggling over by the grill uncontrollably. His suspicions were confirmed that they'd been listening to the interview. He walked her out into the bar. The door opened and Sam walked in, his book bag thrown over his shoulder. Dean heard Becky suck in a breath and almost groaned.

Sam smiled at him and walked closer. Dean grimaced. "Becky, this is my brother, Sam. Sam, this is Becky."

Sam stuck his hand out to shake hers and Dean could have sworn she was about to faint when their hands touched. He didn't think he'd ever seen a smile so wide. _It looks like she fell asleep with a coat hanger in her mouth…_

"Sam…it is _so_ nice to meet you! I hope to be seeing you again soon!"

Sam's smile became somewhat forced and he nodded politely. "Yeah, um, same here."

Becky fluttered her eyelashes at Sam and Dean could have sworn the look she was giving him was rated R. Dean gently moved Becky towards the door. She turned around and smiled at him. "Thank you, Dean. I'll be waiting for your call."

She looked around him and sent a completely unsubtle wink at Sam before turning and leaving. As soon as the door was closed, Dean turned around and scrunched up his face. "I feel dirty…"

Sam's eyebrow rose, but before he could ask, Jo and Benny stumbled into the bar laughing their asses off. Jo was the first one to be able to speak. "Oh my goodness, Dean! That was the best thing ever!"

Dean gagged. "Tonight I'm going to bathe in Purell. You two missed the sultry bedroom eyes she was throwing at Gigantore here. I felt like I was in the middle of a bad porno."

Sam shook his head in confusion, "What in the hell happened?"

Benny spoke up before Dean could. "The whole interview she talked about two brothers having passionate sex and how an angel was breaking them apart, forcing the older brother to love him instead. She called it Wincest!"

Sam's lips parted in confusion and he looked at Dean. Dean shook his head. "Don't say it. Don't even think it. I never want to think about that interview. Ever again."

He shook his head as he reached around the bar and grabbed a beer. He needed one after going through that. "If the next two are as bad as her…I'm making Jo take over the interviewing process."

Jo stopped laughing and stared at him. "You want me to interview more people like _her_? Nope. Not happening."

Dean smirked. "Oh, now it's not so funny, is it?"

She glared at him before shoving Benny back into the kitchen, probably to laugh some more about the interview. Dean turned to Sam before taking a long pull from his beer. "How was school, Sammy?"

Sam nodded, sitting down on a stool. "Good. Classes got out early because some kid pulled the fire alarm as some kind of joke. I'm pretty sure he got arrested or something. So, when's the next interview?"

Dean looked down at his watch. "He should be here in about a few minutes."

He finished off his beer and walked around the bar to throw it away. He leaned against the counter, facing Sam. "If he works out, I might have him start tonight. It should be slow where I can teach him the ropes."

Sam nodded, pulling out his phone to check his messages. "Yeah, tonight should be a good night for that. Let's hope he's not into Wincestrial love."

Dean almost choked on his own spit. He sent a glare Sam's way and almost said something when the door opened and a shorter man with gold locks strolled in. He looked around briefly before looking over at the brothers. He smiled and made his way over. "Hello there, I'm Gabriel Coleman. I have an interview."

Dean smiled politely at him and nodded. "I'm Dean Winchester and this is my brother Sam. Follow me, we'll go back to my office."

Gabriel nodded. He sent a smile Sam's way before following Dean into the back. Jo and Benny stopped laughing when they heard the door open. They looked over to see Dean walk in with a man and were immediately curious. They began their routine of eavesdropping outside the office door as soon as Dean shut it.

Dean sat down behind his desk and pulled out Gabriel's application, skimming it over real quick. "So, let's start with your schedule. When would you be free to work?"

"Anytime, really. I just moved here and have been looking for a job. I saw the ad in the paper and gave it a shot. I don't really have anything else going on to interfere."

Dean nodded, "Okay, good. I'm guessing you're looking for full-time. What position were you wanting?"

"Well, I have previous experience as a bartender in a club back where I moved from. I worked there for about a year before I moved here."

Dean was starting to like the guy more and more. "Alright, awesome. Are you looking for another job to add on top of this one if you get it?"

Gabriel smirked. "No, I'm only looking for one job. If I get this one, I'll stop my search."

"That's good to hear. Less scheduling conflicts. May I ask…why a bar?"

He shrugged, "What can I say? I like being social and what better place to socialize than a bar."

"So, you're a people person. That's a good quality. I just have one more question for you…"

Gabriel nodded, "Shoot."

Dean smirked. "When can you start?"

Gabriel's smirk turned into a grin. "Anytime, Dean-o. I can start right now if you need me to."

Dean nodded, "I'll tell you what…you be here by five tonight and you've got a job."

"That's great! Now, on to more important matters. What's the dress code?"

"Casual. Dark jeans, nice t-shirt, overshirt if you want to. I don't care about the shoes as long as they have traction. It gets a bit slippery."

Gabriel nodded, "That's doable. Do I need to sign anything or am I good to go?"

Dean reached into his desk and pulled out a couple sheets of paper. He explained that they were for insurance purposes. Then he handed him some papers for him to fill out for taxes. "If you want to fill them out here, then you can do that out in the bar at one of the booths. If not, that's fine just bring it back to me as soon as you can."

Gabriel nodded and stood. He reached out and shook Dean's hand. "Awesome! Well, I do have some things to get done and some changing to do, so I will bring them back."

Dean nodded, "Okay, let's go introduce you to the others before you go and then you're all set."

He moved out from behind his desk and lead the way out of the office, back into the bar. He'd noticed Benny and Jo weren't anywhere in the kitchen so he figured they'd run out to tell Sam the good news.

They found Sam, Jo, and Benny huddled around the bar talking. They abruptly stopped when they heard the door to the kitchen open. Dean rolled his eyes but made the introductions. "Jo, Benny, this is Gabriel. Gabriel, this is Jo and Benny. Jo is the waitress and Benny is the cook. They'll both be here tonight."

Gabriel stepped closed to shake their hands. "Please, call me Gabe. Everyone does."

Jo smiled, "It's nice to meet you, Gabe. Looks like we'll be seeing you tonight then?"

He nodded, "Yep! Dean-o here gave me the job. I will see you people here at five! Adios!"

Dean chuckled and watched the short man leave the bar. The three of them turned to him smiling. He raised an eyebrow. "What?"

Jo jumped up and down. "We have a new bartender! Aren't you excited?!"

He rolled his eyes, but couldn't help the smile that graced his lips. "I'll be excited if he doesn't turn out to be some crazy stalker or know-it-all who scares off business."

"You heard him in there! He likes to be social. I don't think he'll be either. So, it's a safe bet that he'll be here to stay."

Dean sat down on the stool next to Sam. "Well, don't get your hopes up. Tonight will be a test run. We'll see how he handles it."

"Dude, he said he was a bartender for almost a year. I think he'll do just fine."

Dean nodded, "I hope so. Anyways, next interview should be here soon. She's the last one, thankfully. If you're lucky, maybe I'll hire her as a waitress."

Jo smiled, "Good! We need another one of those."

"No, I meant to replace you."

She rolled her eyes. "Oh, Dean, you know you wouldn't last a _day _without me."

Sam nodded, "You know, she's right, Dean."

Dean rolled his eyes, "Oh, shut up."

They continued to talk about different things that had been going on in each of their lives. The group hadn't gotten to see each other outside of work in a while, so it was a good time to catch up on things that weren't discussed in passing while at the bar. They wasted a good fifteen minutes laughing at each other before the door opened for a third time. They all turned to see who it was and found a girl, maybe in her late teens, early twenties. She had long red hair, a canvas bag slung across her chest, and converse. Dean had a good feeling about her immediately.

He stood to greet her. "You must be Charlie?"

She nodded. She seemed a bit nervous. "Charlie Bradbury, at your service. You must be Dean?"

He smiled and nodded, "That's me! Why don't we head into my office and we'll get started with the interview."

She nodded and followed him as he left for his office. It was getting to be routine for him now. When they entered his office, he shut the door and took a seat behind his desk like he'd done the last time. He shuffled the applications around until he found Charlie's and looked up at her.

"So, Charlie, tell me about yourself. What brings you here?"

She swallowed, knitted her fingers together and looked up to meet his eye. "Well, I graduated early from high school before I went to MIT. I didn't exactly have the best home situation so I wanted to get out of there as soon as possible. I got a job as this tech person for a company that, frankly, doesn't pay me enough for everything that I do. So, I'm looking for a second job. I'm hoping part-time. I've been a waitress before, but never been behind a bar. I'm hoping to save up enough money to go to this thing I go to every year? It's called Comic-con, you probably haven't heard of it, but it's a lot of fun."

Dean's smile grew. "I've heard of it. Even thought about going one year."

Her face brightened. "Really? What genre? Or is it a bunch of them?"

"Star Wars, Star Trek, Lord of the Rings…that sort of thing."

"Awesome! You're a geek master."

His smile grew even more and he relaxed. He was really liking her so far. "When can you work? I can give you weekends and if you need more I can give you some nights during the week and special events."

Charlie nodded, "That would be great! I could handle a few nights during the week as well as weekends."

Dean nodded, reaching into his desk for the paperwork. "Okay, I'm going to have to have you sign these for insurance purposes and fill these out for taxes. You can take the one for taxes with you and return it to me as soon as you can."

As she was signing the papers, Dean thought back on what she had said. She hadn't had the best home situation and had wanted to get out of there quickly. It reminded him of his own home situation when he was growing up. His mother had died when he was young and his father was an alcoholic that was always either working, sleeping, or drinking. He'd raised Sam all on his own since he was six. He could definitely relate to a bad home situation. Whatever Charlie had gone through…for some reason he wanted to make sure she never had to go through it again. He felt a wave of protectiveness wash over him and he hardly knew the girl. Immediately he knew that she would make a great fit here.

When she finished signing the insurance papers, she looked up at him smiling. "So, when do I start?"

Dean smiled. "Today's Tuesday, so how about you come in tomorrow night about five-thirty? I'd have you start tonight, but I have someone else starting tonight behind the bar and would rather focus on training one person at a time."

Charlie nodded, "Oh, that's completely understandable. Is that all, or is there more I need to know?"

Dean shook his head, standing up. "Nope. Let's go introduce you to the others and I'll let you get on your way."

They walked back out into the bar, following the same routine. He could see the smile threatening to break out on Jo's face and he knew they'd been listening again.

"Jo, Benny, Sam, this is Charlie, our new part-time waitress. Charlie, this is my brother, Sam, Jo, the other waitress, and Benny, our cook."

She smiled at them all and gave them a small wave. "It's nice to meet all of you!"

They smiled back and Jo nodded, "Believe me, it's good to meet you too! When do you start?"

"Tomorrow night at five-thirty."

Jo's smile widened. "Awesome! Well, we'll see you then!"

Charlie gave them all another wave before walking out of the bar. Dean sat down on the stool he'd been sitting at beside Sam. Jo smiled at him. "So. She's a geek just like you. You must be pretty excited to have someone to geek-out over with."

He rolled his eyes. "Shut it, Jo. She's a nice girl and her hours fit perfectly. I think she'll make a good addition."

She nodded, "I agree. She seems really nice. She'll fit right in around here."

Dean didn't know how to respond, so he kept his mouth shut and ran over a mental list of things he needed to get done. His mind began to wander to the two people he just hired. He really hoped that they would work out and that he wouldn't regret it.

**So...what did you think? I had fun writing the parts with Becky, haha!**


	2. Moose

**Disclaimer: I do not own SPN. Krpike does...**

**Summary: Gabe gets an idea and he recruits Sam to help him.**

**Note: Sorry it's been a few days. I kind of got stuck on where to go with it. I already have next chapter planned out, so I hope to get it up much sooner! Well, enjoy!**

**Chapter 2**

"So, Gabe…what made you decide to move to Mountain View?"

Gabe looked up from the glass he was cleaning off and saw Sam looking at him, waiting for an answer. Dean looked over at the two from the corner of his eye, interested in the conversation.

"Oh you know, the view. And my best friend lives here. He moved out here for a job a while back and we're practically brothers so I moved out here first chance I got."

Sam nodded, interested. "That's really cool. It helps knowing someone when you move. Who's your friend? Maybe we know him."

Gabe smirked. "Probably not. He's a bit of a recluse. He's a professor down at Stanford. For being a college professor, he really doesn't know how to live. He stays home all the time and grades papers. Oh, and the courses he teaches? Super boring."

Sam raised an eyebrow. "Well, I go to Stanford so maybe I have him in class or something."

Gabe's smirk turned into a smile. "Smart and handsome. I like that. His name is Castiel Novak. He teaches-."

"He teaches history. I don't have him in class, but he tutors students in different subjects. I had him as a tutor last semester, but now we're friends. I see him all the time."

Gabe's eyebrows shot up. "You mean Cassie has a friend other than me? Wow, small world. He's never mentioned it to me, though we don't exactly talk about his life that much. Or…lack of one. I've been trying to get him to get out more, but you know how it is with him, I'm sure. He'd rather stay home and read a book than talk to a human being."

Sam chuckled, "Yeah, that's Castiel, alright. You should get him to come to the bar sometime, have a beer. I bet he'd enjoy himself."

Gabe nodded, "Yeah, that's a good idea. I'll work on it. You should too. Maybe if two people push him out of the house, he'll actually do it."

"Alright, sounds like a plan! I'm meeting him in a little bit, so I'll see what I can do."

Dean chuckled. It was just like Sam to try and get people to socialize. It was also just like him to stay inside and study his ass off. Dean didn't think the kid had been to a single party in his entire college experience. It didn't surprise him at all that he wasn't dating anyone.

"So, Sam, you said you're going to Stanford. What are you studying?"

Sam took a swig from his beer before answering. "I'm pre-law."

Gabe's eyes widened. "Pre-law? Damn. You're one smart moose."

Dean couldn't keep his laughter under control anymore. He'd never heard anyone call his brother a moose before. The nickname fit so perfectly Dean couldn't control himself.

Sam glared at his brother. "What's so funny, Dean?"

When Dean was able to collect himself, he grinned at Sam. "I've never heard anyone call you moose before. I'll have to remember it. It fits perfectly."

Sam rolled his eyes. "Ha ha, very funny, Dean."

Dean smirked and turned his attention on a group of young ladies sitting at the bar. Gabe watched him out of the corner of his eye as he flirted with the girls and received each of their numbers. He stashed them in his pocket as he walked away from the group. Gabe turned to Sam.

"So, tell me something, Sam. Is your brother a womanizer or is he just overly friendly?"

Sam looked up from his phone and watched as Dean flirted with another young lady as he poured her a shot.

"He flirts with them so they'll buy more drinks. They give him their number, he accepts it, but then later after he closes, he throws them all away. I've never seen him use a single number he's been given."

Gabe's brow furrowed. "Why? They're very attractive and he seems like the type to be a womanizer. Unless…he's got a girlfriend?"

Sam shook his head. "Nope. The last girlfriend he had…well…it didn't end too well. That was about a year ago, I think. I don't think he's been on a single date since."

Gabe watched as Dean flirted with another customer. When he walked away, that look of sheer flirtation melted away and a wall of stone was seen in his eyes. He was hiding something from the world, something not even Sam could see.

"If you don't mind me asking, Samsquatch, but…what happened with him and this chick for him to not go on a single date since?"

Sam looked down at his beer, chewing absently on his bottom lip for a moment before looking back up at Gabe. "Well…her name was Lisa. They were perfect for each other. They'd had a couple of flings before getting together, but when they did get together…they were with each other for a year. That's the longest relationship he's ever had. Everything was great. Dean was the happiest I've ever seen him. They moved in together pretty early in the relationship. Dean even took care of her kid as if he were his own. He loved that kid."

"Okay…so if Dean was so happy, then what happened?"

Sam sighed, "About two months before it ended, Dean mentioned to me that she'd started acting weird. She'd ignore his calls, come home late. He said she was distant. He'd tried talking to her about it, but she just waved it off and said she was stressed at work, there was a lot to do, it wasn't a big deal. He believed her and dismissed it. Then she started getting calls in the middle of the night sometimes where she would take them into the other room. At first, Dean would just go back to bed and not pay any attention to it, but one night he got up and listened to see what was going on. He never told me what he heard, but it made him suspicious. One day he had Ellen cover for him and he followed her after she got off work. He followed her all the way to this little apartment building a couple of towns over. Ben, the kid, was staying at a friend's house so he wasn't with Lisa. He stayed for a little bit, but ended up going home and waiting for her there. When she got home, it was really early in the morning, way later than she'd ever come home. Dean questioned her, told her he was suspicious, asked her to be honest with him. They got into a huge fight and she kicked him out. She accused him of being paranoid and not trusting her. A few days later, Dean and I stopped over when he didn't think she'd be home to get some of his stuff and found her there with another guy. The guy was confused and said, 'Is this that douchebag? The one you kicked out?' It got pretty loud and heated after that. Lisa ended up accidentally admitting to cheating on Dean with the guy, Dean decked him, then we left. Lisa told Dean that if he ever went near Ben again, she'd have him arrested. The only reason he got his stuff back was because I went back later on and got it from her. He found the house he's living in now and hasn't seen anyone since. He was pretty upset that he could never see Ben again."

Gabe's mouth had dropped open halfway through Sam's story and had stayed there until Sam was finished. His eyes were wide and Sam could swear he looked like a fish.

"Damn…no wonder the guy hasn't seen anyone. That's a pretty bad situation."

Sam nodded, finishing off his beer. "Yeah. We gave him some time, but after a while we started to try to get him to see anyone, even go sleep with someone, act like his normal self. He snapped and said it wasn't any of our business what he did with his free time. That was the last time any of us tried to get him back out there."

Gabe nodded, looking over at Dean who was pouring a mug of beer. "Sam…I have an idea."

Sam looked up at him and raised an eyebrow. "Oh, yeah? What's that?"

Gabe looked at him with a grin on his face. "Let's play a little game. It's something I like to call…matchmaker."

Sam just stared at him. "Matchmaker."

"Yes, matchmaker. We are going to find Dean-o a girlfriend. He is going to be happy again."

Sam snorted, "You think you can get him to date someone?"

"Of course I do! I'm an expert. I worked at a club for a year, remember? I did it as a living. You want your brother to be happy again or what?"

Sam looked over at Dean and watched him carefully. He watched the way he moved, tense but not stiff. He was guarded. He flirted, but he didn't let anyone see his true self. He wore a smile, but he wasn't really happy. Sam looked back at Gabe.

"Okay, let's do it."

Gabe held up a finger. "Ah, ah, ah. Only on one condition."

Sam repressed the urge to roll his eyes. "And what might that be?"

"You have to agree to go on a date yourself."

Sam's brow furrowed, not sure if he liked where this was going. "On a date? With who?"

"Me, of course. So, what do you say, Samsquatch. Go on a date with me? I promise you won't regret it."

Sam thought over his options. He knew that Dean wouldn't listen to him, Jo, Benny, or Ellen when it came to dating again, but just maybe if they did it right…Dean would never know it was them who were setting him up.

"I'll make you a deal. If you can find someone who makes Dean happy and he agrees to go on a date with them…then I'll go on a date with you."

A smile lit up Gabe's face and he stuck out his hand. "You have a deal."

Sam smiled when he saw Castiel walk through the doors of the little restaurant they'd chosen to meet up at. He'd only just arrived himself, so he hadn't had to wait long.

Castiel walked over to the table and sat down. "Hello, Sam."

"Hey, Castiel! Get all your papers graded?"

"Yes, I just finished right before I had to leave."

Sam nodded, picking up his beer. "That's good. So, what's been going on lately? Anything new?"

Castiel shook his head. "The only news I have to share is that a good friend of mine has moved to town. He moved here recently from our hometown."

Sam nodded, "Yeah, uh, Gabe."

Castiel's brow furrowed together. "You know him?"

Sam took a swig of his beer before setting it down. "Yeah, my brother Dean just hired him at the bar. Tonight's his third night working there."

Recognition shown on Castiel's face. "He mentioned he got a job at a bar, but that is all I was told. I had no idea that it was your brother's bar."

Sam nodded, "Yep. He started the same day Dean hired him. He's been needing a new bartended for a while now, but was hesitant to hire anyone else. Personally, I think he was just afraid to introduce anyone else into the family. We haven't exactly had the best of luck with bartenders. I think Dean saw some potential in Gabe and gave him the job right away."

Castiel smiled. "Gabriel really needed a job and I am glad he found one so quickly. He has not complained once about it so far, so that is a good sign."

Sam chuckled, "Yeah, he seems to like it. Hey, why don't you come sometime. I'm there a lot so I can see Dean and the others. That's where I was before I came here actually. It'll be fun."

Castiel was about to object, but Sam interrupted him. "Come on, Castiel, have some fun. Just come have a beer with me and then we can go to that bookstore you like so much that is only a couple of minutes away from there."

Castiel thought it over, weighing his options. He wasn't a big drinker, but one drink couldn't hurt. "One beer and then we go to the bookstore?"

A grin appeared on Sam's face. "One beer and then we can go anywhere you want. Just come down and check it out. You won't regret it, I promise."

Castiel chewed his lip for a moment. "Fine. You have a deal, Sam. When would you like to go?"

"How about tomorrow night? We can grab a bite to eat at the bar, Benny's cooking is phenomenal, have a beer, then we can hit the road. I can finally introduce you to my brother too. He's always asking me who you are, trying to make sure I'm not hanging out with a psychotic freak."

"That is very wise of him, Sam. For all he knows I could kidnap you and he may never see you again. Though I would never do that, your brother has every reason to worry."

Sam rolled his eyes. "Yeah, you and him would get along great. I can see it now."

**So...what did y'all think?**


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